p-Toluenesulfonic acid → (R)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate

HRID 1771159

反応式

HRID 1771159 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:17][OH:18])[CH2:13][C:14]([OH:16])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:16]=[C:14]1[O:18][CH2:17][C@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:13]1

参加物

4

反応物 2

HCID 6101p-Toluenesulfonic acidHCID 13340758(R)-3-(((benzyloxy)carbonyl)amino)-4-hydroxybutanoic acid2 回

生成物 1

HCID 697924(R)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate収率 88.6%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

(R)-3-(Benzyloxycarbonylamino)-4-hydroxybutanoic acid (INTERMEDIATE 2, 27.7 g, 109.38 mmol) was dissolved in toluene (648 ml). p-Toluenesulfonic acid (367 mg, 2.13 mmol) was added to the solution and the resulting mixture was heated at reflux under Dean-Stark conditions for 3 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo. Diethyl ether (200 ml) was added, and formation of crystals was observed upon standing. The crystals were filtered in vacuo. The mother liquors were concentrated in vacuo and additional diethyl ether (40 ml) was added. More crystals appeared which were filtered in vacuo. Both sets of crystals combined to give the title product (22.8 g, yield: 83%).

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux under Dean-Stark conditions for 3 hours
  3. concentrationconcentrated in vacuo
  4. additionDiethyl ether (200 ml) was added
  5. filtrationThe crystals were filtered in vacuo
  6. concentrationThe mother liquors were concentrated in vacuo and additional diethyl ether (40 ml)
  7. additionwas added
  8. filtrationwere filtered in vacuo

出典と根拠

ORDレコード
ord-faeee7130fe84da088a14db7b1d278ad
出典データセット
uspto-grants-2016_02
特許番号
US09248140B2

関連ノート

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